1,10-Phenanthroline-based periodic mesoporous organosilica: from its synthesis to its application in the cobalt-catalyzed alkyne hydrosilylation

1,10-Phenanthroline (Phen) is a typical ligand for metal complexation and various metal/Phen complexes have been applied as a catalyst in several organic transformations. This study reports the synthesis of a Phen-based periodic mesoporous organosilica (Phen-PMO) with the Phen moieties being directly incorporated into the organosilica framework. The Phen-PMO precursor, 3,8-bis[(triisopropoxysilyl)methyl]-1,10-phenanthroline (1a), was prepared via the Kumada-Tamao-Corriu cross-coupling of 3,8-dibromo-1,10-phenanthroline and [(triisopropoxysilyl)methyl]magnesium chloride. The co-condensation of 1a and 1,2-bis(triethoxysilyl)ethane in the presence of P123 as the template surfactant afforded Phen-PMO 3 with an ordered 2-D hexagonal mesoporous structure as confirmed by nitrogen adsorption/desorption measurements, X-ray diffraction, and transition electron microscopy. Co(OAc)(2) was immobilized on Phen-PMO 3, and the obtained complex showed good catalytic activity for the hydrosilylation reaction of phenylacetylene with phenylsilane.

Automated summary

This study presents the synthesis of a Phen-based periodic mesoporous organosilica (Phen-PMO) by directly incorporating Phen moieties into the organosilica framework. The immobilization of Co(OAc)(2) on Phen-PMO 3 showed excellent catalytic activity for the hydrosilylation reaction of phenylacetylene with phenylsilane.